111-34-2

Basic information

• Product Name: 1 -(Ethenyloxy)-butane
• Synonyms: n-Butyl vinyl ether;Ether,butyl vinyl (8CI);1-(Ethenyloxy)butane;1-(Vinyloxy)butane;1-Butoxyethene;BVE;Butoxyethene;Butoxyethylene;Butane, 1-(ethenyloxy)-;NBVE;NSC 8264;Vinylbutyl ether;Vinyl n-butyl ether
• CAS NO: 111-34-2
• Molecular Formula: C₆H₁₂O
• Molecular Weight: 100.15888
• EINECS: 203-860-7
• Mol File: 111-34-2.mol
• Article Data: 48

Chemical Properties

• Melting Point: -92℃
• Boiling Point: 93.6 °C at 760 mmHg
• Flash Point: 15°F
• Appearance: clear liquid
• Density: 0.776 g/cm³
• Vapor Pressure: 55.8mmHg at 25°C
• Refractive Index: 1.4
• Water Solubility: 3 g/L (20℃)
• CAS DataBase Reference: 1 -(Ethenyloxy)-butane(CAS DataBase Reference)
• NIST Chemistry Reference: 1 -(Ethenyloxy)-butane(111-34-2)
• EPA Substance Registry System: 1 -(Ethenyloxy)-butane(111-34-2)

Safety Data

• Hazard Codes: F:Flammable
• Statements: R11:; R19:
• Safety Statements: S16:; S33:; S9:
• Hazardous Substances Data: 111-34-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H12O/c1-3-5-6-7-4-2/h4H,2-3,5-6H2,1H3

Synthetic route

dibutyl acetal (871-22-7) + 6,6-Dimethyloenanthsaeure (15898-92-7) → -butyl vinyl ether (111-34-2)

Conditions	Yield
	83%

acetylene (74-86-2) + butan-1-ol (71-36-3) → -butyl vinyl ether (111-34-2)

Conditions	Yield
With sodium hydroxide; cesium fluoride at 135 - 140℃; under 7600 - 10640 Torr; for 3h;	82%
With sodium butanolate at 100 - 150℃;
With potassium n-butoxide; paraffin oil at 180 - 190℃;

(2-butoxy-ethanesulfinyl)-ethene (81577-06-2) → -butyl vinyl ether (111-34-2) + ethenesulfenic acid (2492-74-2)

Conditions	Yield
With potassium hydroxide at 280 - 290℃;	A 68% B n/a

vinyltriethylsilane (1112-54-5) + butan-1-ol (71-36-3) → -butyl vinyl ether (111-34-2) + hexaethyl disiloxane (994-49-0)

Conditions	Yield
With bromine for 4h;	A 65% B 20%

dibutyl acetal (871-22-7) → -butyl vinyl ether (111-34-2) + butan-1-ol (71-36-3)

Conditions	Yield
phosphoric acid at 200℃; Product distribution; various catalysts;	A 12.5% B 16.7%

butane, 1-(1-ethoxyethoxy)- (57006-87-8) → -butyl vinyl ether (111-34-2)

Conditions	Yield
at 300℃; beim Leiten ueber Kaolin;

dibutyl acetal (871-22-7) → -butyl vinyl ether (111-34-2)

Conditions	Yield
With sodium hydrogen sulfate
With phosphoric acid
With palladium asbestos at 300℃;
With boric acid asbestos at 380 - 410℃;

1,1-dibutoxy-2-chloro-ethane (17437-27-3) → -butyl vinyl ether (111-34-2)

Conditions	Yield
With sodium at 150℃;

1-chloro-hexan-3-ol (52418-81-2) → -butyl vinyl ether (111-34-2) + diethylene glycol dibutyl ether (112-73-2)

Conditions	Yield
With sodium hydroxide

chloroethylene (75-01-4) + sodium butanolate (2372-45-4) → -butyl vinyl ether (111-34-2)

Conditions	Yield
at 100℃;

chloroethylene (75-01-4) + potassium n-butoxide (3999-70-0) → -butyl vinyl ether (111-34-2)

Conditions	Yield
at 100℃;

1-(2-bromoethoxy)butane (6550-99-8) → -butyl vinyl ether (111-34-2)

Conditions	Yield
With sodium hydroxide

1-(2-bromoethoxy)butane (6550-99-8) → -butyl vinyl ether (111-34-2) + diethylene glycol dibutyl ether (112-73-2)

Conditions	Yield
With sodium hydroxide

n-butyl 1-chloroethyl ether (3450-47-3) + N,N-dicyclohexyl-N-ethylamine (7175-49-7) → -butyl vinyl ether (111-34-2)

n-butyl 1-chloroethyl ether (3450-47-3) + N,N-dimethyl-aniline (121-69-7) → -butyl vinyl ether (111-34-2) + butan-1-ol (71-36-3)

1,2-dichloro-ethane (107-06-2) + sodium butanolate (2372-45-4) → -butyl vinyl ether (111-34-2)

diethyl acetal (105-57-7) + butan-1-ol (71-36-3) → -butyl vinyl ether (111-34-2)

Conditions	Yield
at 320℃; beim Leiten ueber mit wss. Natronlauge vorbehandeltes Kieselgur;

4-(vinyloxy)butan-1-ol (17832-28-9) → 2-methyl-[1,3]dioxepane (4469-25-4) + -butyl vinyl ether (111-34-2) + Butane-1,4-diol (110-63-4)

Conditions	Yield
With potassium hydroxide at 180℃; Product distribution;

aluminium trichloride (7446-70-0) + 1-(2-chloroethoxy)butane (10503-96-5) + benzene (71-43-2) → -butyl vinyl ether (111-34-2)

dibutyl acetal (871-22-7) + boric acid-asbestos → -butyl vinyl ether (111-34-2)

Conditions	Yield
at 380 - 410℃;

1,1-dibutoxy-2-chloro-ethane (17437-27-3) + sodium → -butyl vinyl ether (111-34-2)

Conditions	Yield
at 150℃;

1-(2-bromoethoxy)butane (6550-99-8) + sodium hydroxide → -butyl vinyl ether (111-34-2) + diethylene glycol dibutyl ether (112-73-2)

2-butoxyethyl N,N-dimethylcarbamate → -butyl vinyl ether (111-34-2) + carbon dioxide (124-38-9) + dimethyl amine (124-40-3)

Conditions	Yield
at 389.6 - 420.5℃; Kinetics;

2-Butoxyethanol (111-76-2) → -butyl vinyl ether (111-34-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylaniline; diethyl ether; PBr3 2: NaOH View Scheme
Multi-step reaction with 2 steps 1: dimethylaniline; diethyl ether; PBr3 2: NaOH View Scheme

vinyl propyl ether (764-47-6) + butan-1-ol (71-36-3) → -butyl vinyl ether (111-34-2)

Conditions	Yield
With [2,2]bipyridinyl; palladium diacetate In acetonitrile at 60℃; for 6h; Reagent/catalyst;

calcium carbide (75-20-7) + butan-1-ol (71-36-3) → -butyl vinyl ether (111-34-2)

Conditions	Yield
With potassium fluoride; water; potassium hydroxide In neat (no solvent) at 150℃; for 13h; Autoclave;

4-tert-butyl benzyl vinyl ether (64022-41-9) + butan-1-ol (71-36-3) → -butyl vinyl ether (111-34-2) + 4-tert-Butylbenzyl alcohol (877-65-6)

Conditions	Yield
With bathophenanthroline; copper diacetate at 120℃; for 24h; Schlenk technique; Inert atmosphere;

-butyl vinyl ether (111-34-2) + propargyl alcohol (107-19-7) → 3-(1-butoxy-ethoxy)-propyne (871-12-5)

Conditions	Yield
With trifluoroacetic acid at 20 - 60℃; for 0.5h;	100%
With hydrogenchloride	78%
With hydrogenchloride	50%

-butyl vinyl ether (111-34-2) + 1-bromo-3-aza-4-oxo-5-thiaheptanoic acid (137914-54-6) → (2-Bromo-ethylcarbamoylsulfanyl)-acetic acid 1-butoxy-ethyl ester

Conditions	Yield
In benzene at 50℃; for 1h;	100%

-butyl vinyl ether (111-34-2) + N-(p-nitrophenyl)-5-methyl-2-methylsulfonyl-3-thiophenecarbohydrazonoyl chloride (165066-12-6) → 5-Butoxy-3-(2-methanesulfonyl-5-methyl-thiophen-3-yl)-1-(4-nitro-phenyl)-4,5-dihydro-1H-pyrazole (165066-17-1)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 4.5h;	100%

-butyl vinyl ether (111-34-2) + Methyl 8-(phenylmethoxy)-4-<<(trifluoromethyl)sulfonyl>oxy>-2-naphthalenecarboxylate (144003-47-4) → Methyl 4-(1-butoxyvinyl)-8-(phenylmethoxy)-2-naphthalenecarboxylate

Conditions	Yield
With triethylamine; palladium diacetate; 1,3-bis-(diphenylphosphino)propane In N,N-dimethyl-formamide at 60℃; for 24h;	100%

-butyl vinyl ether (111-34-2) + methyl [(diphenylmethyl)imino] acetate N-oxide (77486-11-4, 77486-12-5, 160030-82-0) → methyl [5-(n-butyloxy)-2-diphenylmethylisoxazolidin-3-yl]carboxylate

Conditions	Yield
With Eu(fod)3 In 1,2-dichloro-ethane at 20℃; for 6h;	100%
With Eu(fod)3 In 1,2-dichloro-ethane for 6h; Ambient temperature; Yield given;

-butyl vinyl ether (111-34-2) + ethenyltrimethylsilane (754-05-2) → ((Z)-2-Butoxy-vinyl)-trimethyl-silane + ((E)-2-Butoxy-vinyl)-trimethyl-silane

Conditions	Yield
Grubbs catalyst first generation In benzene at 60℃; for 24h; cross-metathesis; Title compound not separated from byproducts;	A n/a B 100%

-butyl vinyl ether (111-34-2) + 7-trifluoromethyl-3-methoxycarbonyl-4H-1,2-benzoxazine (538342-24-4) → C14H17F3O2

Conditions	Yield
In toluene at 120℃; for 8h; Diels-Alder reaction;	100%

-butyl vinyl ether (111-34-2) + 7-cyano-3-methoxycarbonyl-4H-1,2-benzoxazine (538342-25-5) → C14H17NO2

Conditions	Yield
In toluene at 120℃; for 8h; Diels-Alder reaction;	100%

1,1,1-trifluoromethanesulfonic acid 2-methoxyquinolin-8-yl ester (642477-88-1) + -butyl vinyl ether (111-34-2) → 8-(1-butoxy-vinyl)-2-methoxy-quinoline (642478-21-5)

Conditions	Yield
Stage #1: 1,1,1-trifluoromethanesulfonic acid 2-methoxyquinolin-8-yl ester; -butyl vinyl ether With N-ethyl-N,N-diisopropylamine; palladium diacetate; 1,3-bis-(diphenylphosphino)propane In DMF (N,N-dimethyl-formamide) at 60℃; for 18h; Stage #2: With N-Bromosuccinimide In tetrahydrofuran; water for 1h;	100%

-butyl vinyl ether (111-34-2) + 2-[3-(2-hydroxy-2-phenylethyl)trisulfanyl]-1-phenyl-1-ethanol (1278475-40-3) → 2-{3-[2-(1-butoxyethoxy)-2-phenylethyl]trisulfanyl}-1-phenylethyl 1-butoxyethyl ether (1278475-55-0)

Conditions	Yield
Stage #1: -butyl vinyl ether; 2-[3-(2-hydroxy-2-phenylethyl)trisulfanyl]-1-phenyl-1-ethanol With trifluoroacetic acid In 1,2-dimethoxyethane at 20℃; for 12h; Stage #2: With potassium carbonate In 1,2-dimethoxyethane at 20℃; for 1h;	100%

-butyl vinyl ether (111-34-2) → bis(2-bromo-2-butoxyethyl) selenide (1332580-99-0)

Conditions	Yield
With selenium dibromide In tetrachloromethane at -20 - 20℃; regioselective reaction;	100%
With selenium dibromide In tetrachloromethane at -20 - 20℃; regioselective reaction;	98%

-butyl vinyl ether (111-34-2) + ((1-butoxy-2-methylprop-1-en-1-yl)oxy)trimethylsilane (158362-24-4) → butyl 2,2-dimethyl-3-butenoate

Conditions	Yield
With indium tribromide In 1,2-dichloro-ethane at -20℃; for 2h; regioselective reaction;	100%
With gallium(III) bromide In 1,2-dichloro-ethane at 80℃; for 2h; Catalytic behavior; Kinetics; Reagent/catalyst; Solvent; Temperature;	93%

8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one (530084-79-8) + -butyl vinyl ether (111-34-2) → C24H28BrNO4 (1585234-56-5)

Conditions	Yield
With toluene-4-sulfonic acid In tetrahydrofuran; toluene at 20 - 25℃; for 0.5h; Molecular sieve;	100%
With toluene-4-sulfonic acid In tetrahydrofuran; toluene at 20 - 25℃; for 0.5h; Molecular sieve;	100%

-butyl vinyl ether (111-34-2) + 3,3-(ethylene-dioxy)-17β-cyano-17α-hydroxy-19-norpregna-5(10),9(11)-diene → 17α-[(±)1-(1-n-butyloxyl)ethyl]oxyl-17β-cyano-3,3-(ethylene-dioxy)-19-norpregna-5(10),9(11)-diene

Conditions	Yield
With toluene-4-sulfonic acid In tetrahydrofuran at 20℃; for 4h; Cooling; Large scale;	100%

-butyl vinyl ether (111-34-2) + 6-chloro-2,2'-bipyridine-4,4'-dicarboxylic acid dimethyl ester (1344146-04-8) + palladium diacetate (3375-31-3) → 6-acetyl-2,2'-bipyridine-4,4'-dicarboxylic acid di-n-butyl ester

Conditions	Yield
Stage #1: -butyl vinyl ether; 6-chloro-2,2'-bipyridine-4,4'-dicarboxylic acid dimethyl ester; palladium diacetate With 1,3-bis-(diphenylphosphino)propane; sodium hydrogencarbonate In butan-1-ol Inert atmosphere; Reflux; Stage #2: With hydrogenchloride In methanol; water at 20℃; for 0.166667h;	100%

-butyl vinyl ether (111-34-2) + 3-methyl-phenol (108-39-4) → 1-(n-butoxy)-1-(3-methylphenoxy)ethane (93308-46-4)

Conditions	Yield
With trifluoroacetic acid at 60 - 65℃;	99%
With phosphoric acid at 20℃;

-butyl vinyl ether (111-34-2) + 2-bromo-1-phenyl-ethanone oxime (14181-72-7, 17082-13-2, 17082-14-3) → 6-butoxy-3-phenyl-1,2-oxazine (132868-21-4)

Conditions	Yield
With sodium carbonate In dichloromethane for 15h; Ambient temperature;	99%

-butyl vinyl ether (111-34-2) + 2-hexen-1-ol (2305-21-7) → 1-butoxy-1-(hex-2-enyl)oxy-2-iodoethane (154613-93-1)

Conditions	Yield
With N-iodo-succinimide In dichloromethane at -78 - 0℃;	99%
Stage #1: -butyl vinyl ether; 2-hexen-1-ol In dichloromethane at 20℃; for 0.0833333h; Stage #2: With N-iodo-succinimide In dichloromethane at -78 - 0℃; Further stages.;	99%
With N-iodo-succinimide In dichloromethane Addition;

iodobenzene (591-50-4) + -butyl vinyl ether (111-34-2) → 1-(2-butoxy-1-ethenyl)benzene

Conditions	Yield
With poly(N-isopropylacerylamide)-SCS-PdCl; TEA In n-heptane; N,N-dimethyl acetamide; water at 95℃; for 10h; Heck coupling;	99%

-butyl vinyl ether (111-34-2) + phosphonic acid diethyl ester (762-04-9) → O,O-diethyl (2-butoxyethyl)phosphonate (4219-15-2)

Conditions	Yield
With triethyl borane; oxygen In cyclohexane at 20℃; for 54h;	99%

methanol (67-56-1) + -butyl vinyl ether (111-34-2) → 1-(2-iodo-1-methoxyethoxy)butane

Conditions	Yield
With dicloroiodoisocyanuric acid at 20℃; for 0.0166667h; Darkness; regioselective reaction;	99%
With triiodoisocyanuric acid at 20℃; for 0.0333333h;	83%

-butyl vinyl ether (111-34-2) + tri-n-butyl-tin hydride (688-73-3) → <2-Butyloxy-ethyl>-triisobutyl-zinn (51283-48-8)

Conditions	Yield
In neat (no solvent) other Radiation; under Ar; (60)Co-irradiation; 1.5:1 molar ratio (olefine:Sn-compound) ;25°C; GLC;	99%
other Radiation; gamma-radiation;;	99%
other Radiation; gamma-radiation;;	99%
In not given other Radiation; γ-radiation;;

-butyl vinyl ether (111-34-2) + methyl 2-bromo-5-methoxybenzoate (35450-36-3) → methyl 2-acetyl-5-methoxy-benzoate (1217472-06-4)

Conditions	Yield
With triethylamine; palladium diacetate; triphenylphosphine In acetonitrile at 99℃; for 16.5h; Inert atmosphere;	99%

methyl 2-(2-diazo-1,3-dioxohexyl)benzoate + -butyl vinyl ether (111-34-2) → 1-butanoyl-7-endo-buthoxy-5-methoxy-8-oxabenzo[c]bicyclo[3.2.1]octan-2-one

Conditions	Yield
With dirhodium tetraacetate; nickel(II) perchlorate hexahydrate; (R)-N,N'-bis(4-methyl-2-quinolylmethylene)-1,1'-binaphthyl-2,2'-diamine In dichloromethane at 55℃; for 1h; Inert atmosphere; Molecular sieve; optical yield given as %ee; enantioselective reaction;	99%

-butyl vinyl ether (111-34-2) + N-tert-butoxycarbonyl-D-Phenylalaninol (106454-69-7) → (+)-(R)-tert-butyl [1-phenyl-3-(vinyloxy)propan-2-yl]carbamate (1319741-22-4)

Conditions	Yield
With 1,10-Phenanthroline; palladium (II) trifluoroacetate; triethylamine at 75℃; for 12h; Inert atmosphere;	99%

-butyl vinyl ether (111-34-2) + dimethyl 2-(1,3-dioxoisoindolin-2-yl)-cyclopropane-1,1-dicarboxylate (1352653-03-2) → dimethyl 2-butoxy-4-(1,3-dioxoisoindolin-2-yl)cyclopentane-1,1-dicarboxylate

Conditions	Yield
With tin(IV) chloride In dichloromethane at -78℃; for 1h; Inert atmosphere; optical yield given as %de; diastereoselective reaction;	99%

-butyl vinyl ether (111-34-2) + ethyl (E)-4-((2-(3-methoxy-3-oxoprop-1-enyloxy)phenyl)ethynyl)benzoate (1396510-82-9) → methyl (2SR,3SR)-2-butoxy-4-(4-(ethoxycarbonyl)phenyl)-2,3-dihydrobenzo[b]oxepine-3-carboxylate

Conditions	Yield
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,2-dichloro-ethane at 50℃; for 6h; Inert atmosphere; diastereoselective reaction;	99%

2-phenylpyridine (1008-89-5) + -butyl vinyl ether (111-34-2) → C17H21NO

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In toluene at 80℃; for 12h; Temperature; Reagent/catalyst; Schlenk technique; Inert atmosphere;	99%

-butyl vinyl ether (111-34-2) + phenol (108-95-2) → 1-(n-butoxy-1-phenoxy)ethane (20682-70-6)

Conditions	Yield
With trifluoroacetic acid at 60 - 65℃;	98%
With hydrogenchloride In 1,4-dioxane at 25℃; Rate constant; Mechanism; other alcohols;
With sulfuric acid at 20℃;

methyl coumalate (6018-41-3) + -butyl vinyl ether (111-34-2) → methyl 8-butoxy-3-oxo-2-oxabicyclo[2.2.2]oct-5-ene-6-carboxylate

Conditions	Yield
In acetonitrile at 75℃; for 24h; Diels-Alder Cycloaddition; Sealed tube;	98%
In nitromethane at 70 - 80℃; Yield given;

Upstream product

• 105-57-7 Ethane, 1,1-diethoxy- 
• 7647-10-1 Palladium chloride 

Downstream Products

• 20154-03-4 3-(Trifluoromethyl)pyrazole 
• 154471-65-5 1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE 
• 33034-67-2 2-Chloro-4-(trifluoromethyl)pyrimidine 
• 104048-92-2 2-Hydroxy-4-(trifluoromethyl)pyrimidine 
• 197305-97-8 2-Hydrazino-4-(trifluoromethyl)pyrimidine 

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